Glucopyranoside compound

a technology of glucopyranoside and compound, which is applied in the field of glucopyranoside compound, can solve the problems of edema, heart failure, and significant hypoglycemia of antidiabetic agents, and achieve the effect of delayed wound healing

Active Publication Date: 2012-10-11
MITSUBISHI TANABE PHARMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these antidiabetic agents have various side effects.
For example, biguanide compounds cause lactic acidosis, sulfonylurea compounds cause significant hypoglycemia, insulin resistance improving agents cause edema and heart failure, and α-glucosidase inhibitors cause abdominal bloating and diarrhea.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

1-(β-D-glucopyranosyl)-3-(5-ethyl-2-thienylmethyl)benzene

[0238]

[0239]In the above scheme, Me is a methyl group, Et is an ethyl group, TMSO and OTMS are a trimethylsilyloxy group.

[0240](1) 3-Bromo-(5-ethyl-2-thienylmethyl)benzene 1 (211 mg) was dissolved in tetrahydrofuran (2 ml)-toluene (4 ml), and the mixture was cooled to −78° C. under argon atmosphere. To the mixture was added dropwise n-butyl lithium (2.44 M hexane solution, 0.29 ml), and the mixture was stirred at the same temperature for 30 minutes. Then, a solution of 2,3,4,6-tetrakis-O-trimethylsilyl-D-glucono-1,5-lactone 2 (see U.S. Pat. No. 6,515,117) (233 mg) in toluene (5 ml) was added dropwise, and the mixture was further stirred at the same temperature for one hour to give a lactol compound 3. Without isolating this compound, a solution of methanesulfonic acid (0.1 ml) in methanol (5 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Under ice-cooling, to the mixture was ...

example 2

5-(β-D-glucopyranosyl)-1-(4-ethylphenylmethyl)-1H-pyridin-2-one

[0242]

[0243]In the above scheme, tBu is a tert-butyl group, OTIPS is a triisopropylsilyloxy group, and the other symbols are as defined above.

[0244](1) 5-Bromo-1-(4-ethylphenylmethyl)-1H-pyridin-2-one 6 (293 mg) and boronic acid ester of glucal 7 (1.0 g) were dissolved in dimethoxyethane (5 ml). To the mixture were added bis(triphenyl)phosphine palladium(II) dichloride (35 mg) and 2M sodium carbonate (2.5 ml), and the mixture was heated with stirring under reflux under argon atmosphere for 5 hours. The mixture was cooled to room temperature, and the reaction solution was diluted with ethyl acetate, and washed with water. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-70:30) to give glucal derivative 8 (276 mg) as colorless powder. APCI-Mass m / Z 654 (M+H).

[0245](2) ...

example 3

1-(β-D-glucopyranosyl)-3-(benzo[b]thiophen-2-ylmethyl)benzene

[0247]

[0248]In the above scheme, Bn is a benzyl group.

[0249](1) β-m-Bromophenyl-tetra-O-benzyl-C-glucoside 11 (see WO 01 / 27128) (1.00 g) was dissolved in diethyl ether (60 ml), and the mixture was cooled to −78° C. under argon atmosphere. To the mixture was added dropwise t-butyl lithium (1.49 M pentane solution, 0.99 ml), and the mixture was stirred at the same temperature for 10 minutes. Then, a solution of 2-formylbenzo[b]thiophene (286 mg) in diethyl ether (2 ml) was added dropwise, and the mixture was further stirred at the same temperature for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was warmed to room temperature. The mixture was extracted with diethyl ether, the extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-50...

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Abstract

A compound of the formula:wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH2)n— (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

Description

TECHNICAL FIELD[0001]This application is a Continuation of U.S. application Ser. No. 13 / 174,814, filed Jul. 1, 2011, which is a Divisional of U.S. application Ser. No. 13 / 005,757, filed Jan. 13, 2011, which is a Divisional of U.S. application Ser. No. 11 / 045,446, filed Jan. 31, 2005, which issued as U.S. Pat. No. 7,943,788 B2 on May 17, 2011. U.S. application Ser. No. 11 / 045,446 is a Continuation-In-Part of PCT International Application No. PCT / JP2004 / 011312 filed on Jul. 30, 2004, which designated the United States and on which priority is claimed under 35 U.S.C. §120, which claims priority of Provisional Application No. 60 / 491,534 filed on Aug. 1, 2003. The entire contents of each of the above applications are hereby incorporated by reference.BACKGROUND ART[0002]Diet therapy and exercise therapy are essential in the treatment of diabetes mellitus. When these therapies do not sufficiently control the conditions of patients, insulin or an oral antidiabetic agent is additionally used...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/7042A61P3/10A61K38/26A61K31/7056A61K38/28
CPCA61K38/24A61K38/28A61K45/06A61K31/7042A61K31/7056C07H7/04A61K2300/00C07H7/06C07H19/04C07H19/044C07H19/048C07H19/056A61P3/10
Inventor NOMURA, SUMIHIROKAWANISHI, EIJIUETA, KIICHIRO
Owner MITSUBISHI TANABE PHARMA CORP
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